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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Annapolis Guesthouse - Completely Separate Space
2 bedrooms, 3 beds, 1 private bathroom
29 Aug – 3 Sept
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4.87 out of 5 average rating, 215 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
29 Aug – 3 Sept
4.98 out of 5 average rating, 163 reviews
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
11–16 Aug
New place to stay
Guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
16–21 Aug
4.96 out of 5 average rating, 134 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
23–28 Aug
4.92 out of 5 average rating, 13 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
16–21 Aug
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
14–19 Aug
4.94 out of 5 average rating, 31 reviews
Guest favourite
Home in Cape St. Claire
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
12–17 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Guest house in Annapolis
Walk to City Dock & USNA | Designer Eastport Home
2 bedrooms, 3 beds
17–22 Aug
4.98 out of 5 average rating, 44 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 118 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
11–16 Aug
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Home in Annapolis
Hidden Gem! 6 Guests • 3 Bed • 2 Baths • Dogs
3 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 17 reviews
Home in Annapolis
Annapolis House near Naval Academy
4 bedrooms, 4 beds
13–18 Aug
New place to stay
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews